Potassium Permanganate → 4-(Bis(benzyloxy)phosphoryloxy)benzoic acid

Participants

Reaction Steps

To a solution of dibenzyl 4-formylphenyl phosphate (1.00 g, 2.62 mmol) in acetone (50 mL) was added a solution of potassium permanganate (0.837 g, 5.30 mmol) in acetone (40 mL) and water (40 mL) at rt over 1.5 hr. To the resulting purple mixture was poured 10% NaHSO3 in 1N HCl (100 mL) at rt. The purple solution became colorless and extracted with AcOEt (3×60 mL). The combined extract was washed with brine and dried anhydrous MgSO4. The title compound (0.940 g, 90% yield) was isolated as a white solid by ISCO (5% MeOH/CH2Cl2).

Provenance & Evidence